CA1081255A - Stable substituted acrylamides or methacrylamides - Google Patents
Stable substituted acrylamides or methacrylamidesInfo
- Publication number
- CA1081255A CA1081255A CA274,193A CA274193A CA1081255A CA 1081255 A CA1081255 A CA 1081255A CA 274193 A CA274193 A CA 274193A CA 1081255 A CA1081255 A CA 1081255A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- butyl
- methyl
- mole
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000003926 acrylamides Chemical class 0.000 title abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- -1 methacrylic compound Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 19
- 150000004985 diamines Chemical class 0.000 claims abstract description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000376 reactant Substances 0.000 claims abstract description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 4
- 150000001412 amines Chemical class 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 238000000197 pyrolysis Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HSJUCVMTRAUTNQ-UHFFFAOYSA-N 2-methyl-n-[3-(propan-2-ylamino)propyl]prop-2-enamide Chemical compound CC(C)NCCCNC(=O)C(C)=C HSJUCVMTRAUTNQ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- KFDIDIIKNMZLRZ-UHFFFAOYSA-N n'-propan-2-ylpropane-1,3-diamine Chemical compound CC(C)NCCCN KFDIDIIKNMZLRZ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229940063559 methacrylic acid Drugs 0.000 description 3
- NPMAKXHZQFPWHU-UHFFFAOYSA-N n'-tert-butylpropane-1,3-diamine Chemical compound CC(C)(C)NCCCN NPMAKXHZQFPWHU-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- ZNZCBZJTANSNGL-UHFFFAOYSA-N 1-n,2-n-diphenylbenzene-1,2-diamine Chemical compound C=1C=CC=C(NC=2C=CC=CC=2)C=1NC1=CC=CC=C1 ZNZCBZJTANSNGL-UHFFFAOYSA-N 0.000 description 2
- YSALIZGISXWLMY-UHFFFAOYSA-N 2-methyl-n-[2-(propan-2-ylamino)ethyl]prop-2-enamide Chemical compound CC(C)NCCNC(=O)C(C)=C YSALIZGISXWLMY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BFIMWLBHXWBHBQ-UHFFFAOYSA-N 1-methyl-2-propylhydrazine Chemical compound CCCNNC BFIMWLBHXWBHBQ-UHFFFAOYSA-N 0.000 description 1
- ZVPJDSXXHUJNBH-UHFFFAOYSA-N 2-(3-aminopropyl)-4,4-dimethylpent-2-enamide Chemical compound CC(C)(C)C=C(C(N)=O)CCCN ZVPJDSXXHUJNBH-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IUMRWGYGZHKZKF-UHFFFAOYSA-N 2-aminoprop-2-enamide Chemical group NC(=C)C(N)=O IUMRWGYGZHKZKF-UHFFFAOYSA-N 0.000 description 1
- KDRUIMNNZBMLJR-UHFFFAOYSA-N 2-isopropylaminoethylamine Chemical compound CC(C)NCCN KDRUIMNNZBMLJR-UHFFFAOYSA-N 0.000 description 1
- RZRUOQGLPXQNBX-UHFFFAOYSA-N 2-methyl-n-[3-(methylamino)propyl]prop-2-enamide Chemical compound CNCCCNC(=O)C(C)=C RZRUOQGLPXQNBX-UHFFFAOYSA-N 0.000 description 1
- XPZGYHSSNZNGPT-UHFFFAOYSA-N 2-methylidene-5-(propan-2-ylamino)pentanamide Chemical compound CC(C)NCCCC(=C)C(N)=O XPZGYHSSNZNGPT-UHFFFAOYSA-N 0.000 description 1
- FAKVQKOINPDRTH-UHFFFAOYSA-N 4-methylpentane-1,3-diamine Chemical compound CC(C)C(N)CCN FAKVQKOINPDRTH-UHFFFAOYSA-N 0.000 description 1
- CCDJQTZPIUMXRB-UHFFFAOYSA-N 5-(tert-butylamino)-2-methylidenepentanamide Chemical compound CC(C)(C)NCCCC(=C)C(N)=O CCDJQTZPIUMXRB-UHFFFAOYSA-N 0.000 description 1
- KYOFBAOVSXMASH-UHFFFAOYSA-N 6-(tert-butylamino)hex-2-enamide Chemical compound C(C)(C)(C)NCCCC=CC(=O)N KYOFBAOVSXMASH-UHFFFAOYSA-N 0.000 description 1
- 101100008048 Caenorhabditis elegans cut-4 gene Proteins 0.000 description 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- 235000006696 Catha edulis Nutrition 0.000 description 1
- 240000007681 Catha edulis Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 229940058307 antinematodal tetrahydropyrimidine derivative Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003250 coal slurry Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- MFJWXKGLUBROCW-UHFFFAOYSA-N n-[3-(tert-butylamino)propyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCNC(C)(C)C MFJWXKGLUBROCW-UHFFFAOYSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000005326 tetrahydropyrimidines Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1866—Catalysts containing secondary or tertiary amines or salts thereof having carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/668,171 US4031138A (en) | 1976-03-18 | 1976-03-18 | Stable substituted acrylamides or methacrylamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081255A true CA1081255A (en) | 1980-07-08 |
Family
ID=24681286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA274,193A Expired CA1081255A (en) | 1976-03-18 | 1977-03-17 | Stable substituted acrylamides or methacrylamides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4031138A (enExample) |
| JP (1) | JPS52113915A (enExample) |
| CA (1) | CA1081255A (enExample) |
| DE (1) | DE2656682C2 (enExample) |
| FR (1) | FR2344525A1 (enExample) |
| GB (1) | GB1549950A (enExample) |
| NL (1) | NL175057C (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2809102C2 (de) * | 1978-03-03 | 1986-12-04 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Herstellung von α,β-ungesättigen Carbonsäureamiden |
| US4180643A (en) * | 1978-11-16 | 1979-12-25 | Texaco Development Corp. | Acrylamide or methacrylamide quaternary compounds |
| DE2967510D1 (en) * | 1978-12-27 | 1985-10-10 | Stockhausen Chem Fab Gmbh | Polymers of alpha-beta-unsaturated n-substituted carboxylic-acid amides and their use as sedimentation, flocculation, dewatering and retention auxiliary agents |
| US4212820A (en) * | 1979-04-23 | 1980-07-15 | Texaco Development Corporation | Acrylamide or methacrylamide alkoxypropyl quaternary compounds |
| FR2438668A1 (fr) * | 1979-10-04 | 1980-05-09 | Texaco Development Corp | Procede et catalyseur derivant du methacrylamide pour produire des polyurethanes |
| US4267372A (en) * | 1979-10-26 | 1981-05-12 | American Cyanamid Company | Preparation of N-substituted acrylamide monomers having cationic substituents |
| US4256666A (en) * | 1979-10-29 | 1981-03-17 | Texaco Development Corporation | Preparation of β-aminopropionamides |
| US4259259A (en) * | 1979-11-15 | 1981-03-31 | Texaco Development Corp. | Preparation of β-aminopropionamides |
| US4251461A (en) * | 1980-01-17 | 1981-02-17 | Texaco Development Corporation | Process for reducing acid impurity levels in N-(tertiaryaminoalkyl)acrylamide production |
| US4287363A (en) * | 1980-09-02 | 1981-09-01 | Texaco Inc. | Preparation of N-(alkylaminoalkyl)acrylamides |
| US4393237A (en) * | 1981-07-02 | 1983-07-12 | Texaco Inc. | Polyoxyalkylenepolyacrylamides |
| US4536600A (en) * | 1981-07-02 | 1985-08-20 | Texaco Inc. | Polyoxyalkylenepolyacrylamides and the preparation thereof |
| DE3128575C2 (de) * | 1981-07-20 | 1983-11-17 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Herstellung von N,N'-disubstituierten 3-Aminopropanamiden |
| DE3209800C2 (de) * | 1982-03-18 | 1990-03-08 | Chemische Fabrik Stockhausen GmbH, 4150 Krefeld | Verfahren zur Herstellung von N-(tert. Aminoalkyl)acrylamiden |
| US4675441A (en) * | 1983-09-23 | 1987-06-23 | Texaco Inc. | Preparation of N-substituted acrylamides |
| FR2590567B1 (fr) * | 1985-11-27 | 1988-07-15 | Charbonnages Ste Chimique | Nouveau procede de synthese de (meth)acrylamide de n-dialkylaminoalkyle |
| JP4607469B2 (ja) * | 2003-01-29 | 2011-01-05 | 三洋化成工業株式会社 | ウレタン樹脂及びその粉体の製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567836A (en) * | 1949-06-23 | 1951-09-11 | American Cyanamid Co | Polymers of quaternarized acrylamido compounds as anion exchange resins |
| US2595907A (en) * | 1950-12-30 | 1952-05-06 | American Cyanamid Co | Polymerizable and polymerized acrylonitrile-dialkylaminopropylacrylamide compositions |
| US3671472A (en) * | 1968-10-07 | 1972-06-20 | Rohm & Haas | Mineral-coating compositions comprising an amine polymer and an amylaceous substance and papers coated therewith |
| GB1299012A (en) * | 1969-02-25 | 1972-12-06 | Mitsubishi Gas Chemical Co | Process for producing cationic synthetic latices |
| US3666810A (en) * | 1969-06-11 | 1972-05-30 | Lubrizol Corp | Novel n-3-aminoalkyl amides, polymers thereof, and method for their preparation |
| US3661868A (en) * | 1970-05-01 | 1972-05-09 | Dow Chemical Co | Flocculant |
| US3652671A (en) * | 1970-06-01 | 1972-03-28 | Dow Chemical Co | Process for making a cationic methacrylamide |
| US3878247A (en) * | 1974-01-25 | 1975-04-15 | Jefferson Chem Co Inc | Preparation of n-(tertiaryaminoalkyl) acrylamides |
-
1976
- 1976-03-18 US US05/668,171 patent/US4031138A/en not_active Expired - Lifetime
- 1976-12-15 DE DE2656682A patent/DE2656682C2/de not_active Expired
-
1977
- 1977-01-14 GB GB1429/77A patent/GB1549950A/en not_active Expired
- 1977-02-15 JP JP1468077A patent/JPS52113915A/ja active Granted
- 1977-02-18 NL NLAANVRAGE7701719,A patent/NL175057C/xx not_active IP Right Cessation
- 1977-02-22 FR FR7705024A patent/FR2344525A1/fr active Granted
- 1977-03-17 CA CA274,193A patent/CA1081255A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL175057C (nl) | 1984-09-17 |
| FR2344525B1 (enExample) | 1982-02-19 |
| FR2344525A1 (fr) | 1977-10-14 |
| US4031138A (en) | 1977-06-21 |
| DE2656682A1 (de) | 1977-09-22 |
| GB1549950A (en) | 1979-08-08 |
| NL7701719A (nl) | 1977-09-20 |
| DE2656682C2 (de) | 1984-09-13 |
| JPS52113915A (en) | 1977-09-24 |
| NL175057B (nl) | 1984-04-16 |
| JPS6110460B2 (enExample) | 1986-03-29 |
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